September 23, 2017 Saturday

from: WrySmile 
to: Sassy
date: Sat, Sep 23, 2017 at 10:53 PM
subject: A few things

Hey Sassy,

Can we schedule more time to talk? Maybe Tues or Wed evening or next weekend? I like talking with you and I also want to hear more about local project stuff.

2: I’m going to have to remove some big things from my GDrive. Please download the movies you like and let me know so I can delete them.

3: I’ve posted a longish story for your entertainment (and mine) on my GDrive. Let me know what you think.

I hope to see you soon.

Darrin

PS: What year did you graduate from college? I think you and my wife were there at the same time.

September 20, 2017 Wednesday

from: Sassy
to: WrySmile 
date: Wed, Sep 20, 2017 at 7:23 PM
subject: Re: The Storm

Hiya Darrin! Hope you stayed dry today. Seems like we got off easy on the tropical storm thing.

Have you written erotica taking the woman’s point of view? My brain just churns it out… male view, female view, overview… no clue where it comes from – glad to have a man say it’s readable. Share whatever, whenever.

Let’s think about next week? I’m off this weekend for my high school reunion, and I need to prep. Maybe an evening next week? Or over the weekend of Sept 30-31 for an afternoon? What would you like to do? I feel very comfortable with the idea of talking, and eating… still not sure about anything else. You are such an interesting man, can’t resist hearing more of your stories!

-S

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from: WrySmile 
to: Sassy
date: Wed, Sep 20, 2017 at 8:10 PM
subject: Re: The Storm

Hey, Sass,

Did it rain today? I spent the day in a hermetically sealed office building stepping out only to buy a double espresso.

When I was thinking about you earlier today, I realized one of the reasons I enjoy our conversations (voice

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from: WrySmile 
to: Sassy
date: Wed, Sep 20, 2017 at 8:55 PM
subject: Re: The Storm

oops.. I usually put in a junk email recipient so I don’t accidentally hit send. oops… continuing,

When I was thinking about you earlier today, I realized one of the reasons I enjoy our conversations (voice and email) so much. You are the only person (possibly in my life) that I can be completely open with. I feel comfortable talking about the good and the bad, the intimate details of my inner life that I’ve never shared — even with my beloved wife. For who else would I dare sneak an anal sex double entendre in middle of a nearly innocent sentence? (Don’t tell me you missed it!)

Intimate without “intimacy”… hmnnn!

And that’s without even mentioning what I enjoy about you. Let’s talk more and soon. Tuesday and Wednesday evenings are possible, but only for an hour or two at most.

The afternoons of 9/30 and 10/1 (not 9/31, silly Sassy) will work. There’s a Jazz festival I hope to attend on 9/30. If my wife (let’s call her “Sue”) doesn’t want to go, maybe we can attend together. You pick. Sue is going to be out of town a lot in October, so scheduling will get easier.

(BTW, we’re going to see Gypsy next weekend. [Remember the cast member I spoke to on the bus?])

…

The vibrator story is the closest I’ve come to writing from a woman’s point of view. I’ve tried but it always comes out clichéd. I might try again.

I’m trying to write the story of my time with a college friend. (I was her first lover; cunnilingus was a new idea for her. [I’ll always remember her saying “WHAT ARE YOU DO –oo–ooing?… Oh god!”] I think she was already in love with me, but that wrapped it up tight.) Anyway, maybe I’ll try to flip it around and write from her point of view.

Let me know when you’d like to talk again.

Darrin

PS, did you enjoy the videos I sent you? Let me know if there are any you particularly liked; I might be able to share more like it.

September 19, 2017 Tuesday

from: Sassy
to: WrySmile 
date: Tue, Sep 19, 2017 at 7:18 PM
subject: Re: A Feast.

Well well well… this email was full of treats!

I had a wonderful time talking and walking with you on Sunday! You are a wonderful storyteller. Thank you for getting me back to Tosci’s after far too long, showing me a new park, and your old neighborhood!

And this feast story? Yummy! I am pulsing inside. Whee!

I’ll send you another of mine. This is fun!

-S

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from: Sassy
to: WrySmile 
date: Tue, Sep 19, 2017 at 7:23 PM
subject: The Storm

The Storm

He made it inside just as the first thunder clap sounded. BANG! It started to pour as he walked past the living room windows. Wow. That was close. He loved thunderstorms! He was very tempted to stand outside to watch the storm. Maybe even dance in the downpour. But there was something more important he had to do.

He knew where to find her. He shed his clothes as he made his way to the bedroom and sure enough, there was this lump the size of a person under the blanket. He rubbed where he thought a leg might be, and a slight whimper filtered out through the covers. There was a crash of lightning and another big boom, and she shrieked.

“It’s okay. You’re okay. I’m here,” he said calmly, trying to be soothing. He crawled into the bed next to her. She clung to him and wrapped herself around him, burying her head in his chest, trembling. He couldn’t believe she was still such a wuss about thunderstorms. She was so brave about almost everything else.

But he knew how to distract her. He put his hands on her back and rubbed gently. He explored up and then down, surprised that she was naked. He pressed her ass so that she fit tightly against him. She moaned sweetly when she felt him hard against the top of her leg. She shifted her head up and grabbed his head with her hands, kissing him frantically. He slowed her down a bit, pressing his tongue into her mouth at a leisurely pace and making more soothing noises.

“We have plenty of time…” he pointed out, squeezing her breast and teasingthe nipple.

“Fuck me,” she whispered fiercely. It sent a shock wave through him. He loved it when she talked dirty to him. Everyone else saw her as an ultra-polite, demure lady. Only he knew about the wild girl inside. She was turning the intense fear into another emotion, putting it to good use. Smart girl.

“Yes, ma’am…” he chuckled. He hugged her, pondering which position would be best.

“Fuck me now,” she urged him. She wasn’t going to let him go slow today. She flattened him onto the bed, straddled him and pressed him close, shifting her hips to rub him against her. He could feel her dripping already. It made him a little crazy. He shifted slightly and she took him inside her and began to move. Up and down she went. He put a hand on her hip and one on her breast, twisting, teasing…

He knew her inside and out, as much as any person can know another. But it never stopped surprising him how tight and hot she was, how he fit inside her like a sculptor had made him to be there and made her to make him feel so incredible every single time. When he first touched her as a green boy, he realized that she was different. He had felt an emotional connection for ages, but when they finally kissed, he felt a physical connection to her that he never felt again in his life. Special, comfortable, exciting… and at times, inflammatory. Chemistry. That had never changed. He thought he would get tired of her, stop thinking about her, stop wanting her… but it never happened. Sometimes it drove him crazy, when he couldn’t get to her. When he could and he couldn’t get inside her fast enough. But it was the best kind of crazy… it made him feel alive. Kept him young. Made them both happier than anything or anyone else. And the most amazing thing was that she felt the same way. He marveled over that every day.

She stopped moving… sensing that his mind had drifted. He snapped back to her body and what she was doing, putting a finger at the top of her slit and flicking her most sensitive spot. She sighed in pleasure and started moving again, rising up, arching her back and driving down on him again, shoving him so deep inside…. and then out again. Her tits looked amazing when she did that! It was the sweetest form of torture… so hot, so wet, so…. hmmmm.. he could not think when she was like this. He could feel… oh, man could he feel! Every nerve in his body was on fire. And he craved the heat. She kept turning up the temperature… taking him closer and closer… and then stopping. She was panting. She leaned over and kissed him again, sucking his tongue, twisting her hips… damn. He felt the magic start. He wasn’t going to last long if she kept this up… it was as if every muscle inside her was trying to squeeze him, milk him… whoa, baby. What a woman…he thought she was going to make him peak. But when he thought he couldn’t take it another moment, she stopped, flipping over onto her back on the bed.

She lay there breathing loudly. He tried to figure out what she was up to. She turned to him and kissed him, wrapping herself around him on her side. She stroked him, then put her hand lower, caressing his balls, pressing the spots she knew would send him soaring. His breath grew ragged.. what would she do next?

She pressed a finger inside his ass. Oh, wow… she was really trying to push all his buttons this time! His hips rocketed off the bed. She pumped in and out, whispering in his ear. “You like it when I fuck you, don’t you, fella? Like it when I give your ass the love, eh?” she said, making a little sucking sound. He moaned. She knew just what to do. She moved down his body, putting her mouth where her hand had been, licking his cock and sucking it deep into her mouth, then kissing his balls and sucking them and finally sticking her tongue in his ass! He moaned and trembled. She could be such a vixen!

That was it. He rolled over, pulled her legs up to his shoulders, and dove back inside her, pumping, deep, long strokes while she moaned and then screamed, her head thrashing from side to side. He watched her shake, felt her hips crashing up against him. She opened her eyes and the look… the look nearly made him explode. So many words popped into his head… lust, passion, fire… love. No one loved him like she did. Her mind, her body… it all went together to make him know… mmmm….

There was another big thunderclap and she jumped. He went wild on her, his hips thrusting in and out, hearing the slap of his balls on her skin and her moans… he let go, let his body take over, let the pulsing inside her trigger the flow…. he filled her, shooting over and over inside her, grunting and moaning and… exploding. He collapsed beside her, feeling his heart beat, listening to her breathing… smiling. He did love thunderstorms! And her…

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from: WrySmile 
to: Sassy
date: Tue, Sep 19, 2017 at 7:58 PM
subject: Re: The Storm

Very nice. And told from the man’s point of view! Nicely done.

I’ve got a few more stories started, but they’re not ready for sharing — well, maybe one is close. Let’s keep trying.

When do you want to meet again?

I’m working on my reluctance, but it’s been two steps forward, one back. And sometimes two back. Maybe you could find some ways to encourage me, grease the skids, so to speak

I hope you’re having a good week.

When will you have time to talk more?

Darrin

September 18, 2017 Monday
from: WrySmile 
to: Same Sassygirl 
date: Mon, Sep 18, 2017 at 9:51 PM
subject: A Feast.

Sassy,

I truly enjoyed our time together. You’re interesting, fun and clever. I hope we get a chance to continue our conversation soon.

I finished cleaning up another story for you. I hope you enjoy it and that you send some of yours to me.

Darrin

————

A Feast

We talk on your couch, accompanied by the quiet moans and gasps of a porn video. We sit close to each other, drinking wine and making snide comments about the activity on the screen. Her makeup is wrong. I’ve never seen one so big. Those are definitely not natural. Now and then you stroke my arm or my knee; I stroke the back of your hands, your thigh, your side.

We share a joint and start to make out, kissing, rubbing and nibbling each other. We remove each other’s shirts and pants. I push you back on the couch and kiss your mouth and nuzzle your neck. You pull my right hand to your left breast; I gently squeeze and massage your breast and play with your nipple. My mouth moves slowly from your mouth and neck to your chest, the space between your breasts. I inhale deeply, enjoying your earthy scent.

My mouth moves to your right breast; I kiss and suck the nipple through the bra while squeezing your left breast firmly. You hold my head, occasionally pulling me closer to your breast, sometimes running you fingers through my hair.

I look you in the eye and we again kiss passionately, my right hand firmly massaging your left breast, your right hand holding onto my hard cock. I again kiss and taste your neck; moving up your neck I approach your ear. I squeeze your breast firmly and gently pinch your nipple as I give you a light lick in your ear and exhale lightly. You giggle and shiver.

I straddle you, sitting on your belly and lower ribs, kiss your kips passionately, then nuzzle your neck. As I lean forward my cock rubs against you. Then I hold both of your hands back over your head. I kiss, lick and nibble your throat and rub my cock between your breasts. I lie down on top of you and slowly taste you from collarbone to earlobe. Letting go of one hand, I squeeze your left breast hard while I flatten my wet tongue against your ear and lick your ear from earlobe to top.

You cry out, wiggle and squirm, but I pin you down, squeezing your breast, pinching your erect nipple, flutter-licking and blowing into your ear. Your body bucks, “Oh god. No! Stop!” but you’re clearly loving it. I stop and kiss your neck and mouth; you look both relieved and disappointed. So I pull down my briefs to let my erection loose and bring it to your lips.

Have you ever had a puppy? You’re both in the kitchen; she’s hungry and excited, knowing she’s about to be fed. She jumps against your leg excitedly, whimpering and giving little barks of anticipation. Then you feed her hamburger and her excitement redoubles, wiggling with excitement, she can barely contain her joy. Occasionally she glances up at you with gratitude.

That was your reaction to my cock at your lips. You sucked my hard penis into your mouth and out and in, occasionally making sounds of joy and looking up at me to see how much I’m enjoying it. (Immensely!) Squeezing the base while your lips move up and down and up and down then down your throat!! (I almost scream with pleasure.) You suck a few more times and back down your throat while you cup and stroke the underside of my balls. And again and again and again. It couldn’t have been more than 10 minutes, bit it felt like lifetimes – I had lost my sense of time, of anything, really, other than the overwhelming pleasure of your hand lips, mouth, tongue and throat.

After a little while, you ease off and push me onto my back, panting. You remove your bra and your wet panties. You rub, kiss and lick my face and body, sometimes holding or stroking my cock. Then you straddle my head and say, “My turn.” I don’t need convincing.

There’s nothing subtle about your approach: facing away from my cock, you drop your vulva on my lips almost before I can open my mouth and start to pump. I lick slowly and probe your labia and vagina with my tongue. My licking gets a little faster as I grab your buttcheeks in both hands and pull you onto my mouth with a rhythm that matches my tongue. Sometimes I grab your cheeks harder and my licking speeds up, up and down, side to side; then back to a slower rhythm again.

You moan and start rocking back and forth in your own rhythm. I slide my hands gently over your sides and up to your tits. I lick faster as I squeeze your right breast while I roll your left nipple between my fingertips. I ease off, then get more intense, three or four times; during the next ease off I slide first one, then two fingers in your vagina. I nibble your labia while my fingers slowly fuck your pussy, then I lick your clitoris gently. You moan and gasp repeatedly.

You’re really getting hot, grunting, pumping your pussy onto my mouth… so I slow down my fingers and my tongue. I roll you on your back, my two fingers deep and still in your very tight vagina. I lick my way from your pubic hair across your belly up to your breasts. I lick my way around your right breast spiraling in from the perimeter towards the nipple. I give your nipple a few slow licks, with my tongue flat and wide; my fingers gently start moving inside your pussy. Your breathing speeds up, I move my fingers firmly in and out and in and out while I suck your nipple hard and gently rub slide it in and out between my teeth. Your back starts to arch; you cry out.

But I slow to a stop and let you catch your breath. I gently remove my fingers from you wet cunt and slowly start to lick and stroke my way back to your erogenous center. My hand is holding your mound as I spend a long time licking, stroking and running my beard over your belly, hips, knees, the inside of your thighs. You smell and taste like deep pleasure, matching you gentle gasps and sighs. You reach for my hard cock, but I don’t let you.

Then without warning, my mouth is on your vulva again. My left hand is squeezing a butt cheek rhythmically as I start licking – slowly, but not gently. My fingers slide into your cunt again, slowly, but not gently. Your gasps, moans and movements tell me that the time is coming. My licking and pumping grow faster (and less predictable). Your moans are almost constant. My fingers pump deep and fast, my tongue flutters wildly.

And I slide a finger into your butthole and start to pump slowly.

That pushes you over the edge. Far over the edge! You thrash, pump your hips, cry out unintelligibly and loud as I pumping fingers into your cunt and your asshole, rapidly flutter-licking your clit. Until your back arches hard, your body spasms three or four times as you yell, “FUCK. FUCK! FUCK FUCK!FUCKFUCKFUCK FUCKFUCK!!!!” You fall back to the bed, panting and quivering.

This time, when you reach for my cock, I let you.

September 14, 2017 Thursday

Ashley Madison Message

Date: Sep 14th – 2:24pm
From: Sassy
To: WrySmile

Message
Hiya Wry! How’re you this warm day?

I am having a wacky day at the office but decided to take a break and write to you! Thank you for your message! And the photo. Adore a man who still has hair on his head and a beard!

Give me a little time to get to know you before I jump to email and share a photo?

Three quick questions –

What’s your favorite ice cream flavor.

How did you hear about it? (I’m curious as well as Sassy!)

When did you first have sex?

Here’s more about me – I am not into vanilla… I like butter pecan! Nuts are so yummy. 😉 I’m on AM because Hubby and I are great friends, but we haven’t had sex in a long time. He does his thing and I do mine. He’s fine with that. I heard about AM while reading a blog by a guy who shared his adventures pleasing married women and himself. And I’m here because I beat cancer six years ago. I’m whole and healthy, and want to live life to the fullest! I am an office manager by day. You know – that shy, demure, efficient lady who takes care of the administrative tasks so the senior staff can focus on the business. Men say I am an awesome kisser, a great communicator, discreet, no drama, super-nice… looking for fun and passion and a confidante. Is that you?

Finally… please feel free to ask me whatever you like to see if we click, and tell me more about you.

Hugs with groping! -Sassy

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Date: Sep 14th – 10:36pm
From: WrySmile
To: Sassy

Message
Responses #1. (I enjoy writing.)
Favorite Ice Cream: I would normally say Toscanini’s burnt caramel, but I had some basil ice cream at a fancy (“artisanal”) restaurant that sent me to the place where poets get their inspiration. Unfortunately, I probably can’t afford to go back there for a long time, so I’ll stick with burnt caramel.

How did I hear about it? I used to live near Toscanini’s, and went there frequently (clearly I was much younger). I tried burnt caramel and was sold instantly.

(I have to tell you: when I skimmed your message I thought you were asking me how I heard about sex! That was probably from Marc Schalater in junior high school. Of course he really didn’t know anything.) I first had sex second semester freshman year in college on a mattress on the floor of my room. Donna was one of my best friends in high school, but we didn’t start dating until I was in college (she was still in high school). She came up to visit and we finally got our chance. It wasn’t good – worse for her.

“Nuts are so yummy.” Did you intend the double-entendre?

I’m not much of a groper – I’m more of a hugger/caresser. You might have to demonstrate. Am I an awesome kisser? I have no idea. But I’m a respectful lover, always reading and responding to my woman’s reactions and level of arousal. Am I a great communicator? I guess so: I’ve been called a great listener and a great conversationalist.

Discreet, no drama? Definitely!

Super-nice: I’m confident that you’ll find that I am.

Looking for fun and passion and a confidante. Definitely. My wife and I do less together, don’t share passion together and talk to each other a lot less than we used to. And there are things we don’t talk about – like sex and what I do on the web. I want to fill in all of those gaps.

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Date: Sep 14th – 11:04pm
From: WrySmile
To: Sassy

Message
BTW: I never said thank you for your great reply. Thank you.

More about me: I’m generally quite modest, respectful, open and friendly. I’m very analytical and VERY verbal. I love to meet people and I love to make them laugh. I’m not a man’s man or a ladies’ man. Throughout my life, many of my closest friends have been women who were not also lovers. My work history is all over the place – [redacted impressive list of professional office positions] and [current job]. It sounds much more impressive than the reality. I’m one of the least impressive graduates of two very impressive universities.

My wife and I love each other: we hug, kiss and hold hands. But she lost interest in sex years ago and gave it up completely soon after that. The last time I had sex with a woman other than my wife was 1979. So I’m badly out of practice. But I think I’m still pretty good; as Woody Allen wrote: “Countess Alexandrovna: You are the greatest lover I’ve ever had.

Boris: Well, I practice a lot when I’m alone.”

My wife knows about my “practicing” and has no problem with it, but also no interest.

——– Questions for you: > Have you had affairs? > When was the first time you had sex > When was the last time you had sex > When was the first time a lover gave you a powerful orgasm? How did it happen? > What kind of porn do you enjoy? > Please name some of your favorite movies

Please respond to items in my wish list: > Enjoys jazz and “serious” movies (e.g. “Spotlight”) > Has eyes I can get lost in > Loves long sessions (10 minutes +) receiving oral sex [I think I know the answer to this] > Makes me laugh [We already know the answer] > Hates most current comedies; thinks action movies are mostly boring > Has a nice butt > Enjoys giving head [We know the answer to this too] > Politically liberal or, if not, enjoys a good debate > Enjoys back door play or is willing to experiment > 420 friendly